Keeping in touch without being annoying
You meet someone good. Neither of you needs anything from the other. Eleven months later you do, and by then you are a stranger with an agenda.
The whole problem is the year in the middle.
Do not use a CRM for this
Founders reach for a system, tag everyone, set quarterly reminders, and then send quarterly messages that read exactly like quarterly reminders. People can tell. A scheduled "just checking in" is worse than silence because it is silence with admin attached.
What works is smaller and less organised.
Send things, do not check in
The only reliable format is sending something specific, with no ask attached.
Saw this and thought of what you said about no-shows.
One line, one link. No question, no meeting request, no suggestion of a call. It takes forty seconds and it keeps you present without costing them anything to receive.
If you cannot think of something to send, that is the signal that you have nothing to say, and you should not send anything.
React in public occasionally
Low effort and genuinely effective: a real comment on something they wrote. Not "great post". A sentence that shows you read it and have a view.
Three of those a year will keep you more present than any amount of private messaging, and they are visible to everyone else too.
Be specific when you finally do need something
When the moment arrives, do not pretend the year did not happen. Name it:
We met at the Foundry dinner about a year ago, and I have been reading your stuff since. I am writing now because [specific thing].
Acknowledging the gap is disarming and honest. Pretending you have been close is transparent and slightly insulting.
Pick a small number
You cannot keep in touch with two hundred people and the attempt produces the robotic version. Pick fifteen you genuinely want in your life in five years, and let the rest be people you were glad to meet.
Fifteen is a number you can actually think about. Two hundred is a spreadsheet, and spreadsheets produce quarterly check-ins.